Convenient synthesis of <i>N</i>-alkyl-3,1-benzoxazin-2-ones from carbamate protected anthranil aldehydes and ketones <i>via</i> one-step alkylation/alkoxy rearrangement.

Tian, Guang; Jin, Wei-Li; Qin, Chuanguang; Wang, Jie

Convenient synthesis of N-alkyl-3,1-benzoxazin-2-ones from carbamate protected anthranil aldehydes and ketones via one-step alkylation/alkoxy rearrangement.

Tian, Guang; Jin, Wei-Li; Qin, Chuanguang; Wang, Jie.

Afiliação

Tian G; Department of Chemistry, Shanxi Key Laboratory of Polymer Science & Technology, MOE Key Laboratory of Supernormal Material Physics & Chemistry, School of Chemical & Chemical Engineering, Northwestern Polytechnical University, Xi'an 710129, China. qinchg@nwpu.edu.cn.
Jin WL; State Key Laboratory of Chemical Biology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China. jiewang@simm.ac.cn.
Qin C; School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing 210023, China.
Wang J; State Key Laboratory of Chemical Biology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China. jiewang@simm.ac.cn.

Org Biomol Chem ; 21(28): 5757-5761, 2023 Jul 19.

Article em En | MEDLINE | ID: mdl-37404025

ABSTRACT

ABSTRACT

A practical and step-economical protocol was developed to prepare N-alkyl-3,1-benzoxazin-2-one derivatives from anthranil aldehydes and ketones via one-step alkylation/alkoxy rearrangement, where three new chemical bonds and one ring were constructed in a single step. Control studies revealed a stepwise mechanism and that the alkoxy rearrangement was an intermolecular process.

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Tipo de estudo: Guideline Idioma: En Revista: Org Biomol Chem Assunto da revista: BIOQUIMICA / QUIMICA Ano de publicação: 2023 Tipo de documento: Article País de afiliação: China

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